H. Upmann is among the oldest cigar brands in existence, dating back to the 1840s. Around 1840, banker Herman Upmann opened a branch office in Havana, which provided ample opportunity to send cigars home to Europe.[1] The possibilities of a commercial endeavor became clear to Upmann and in 1844 he invested in a cigar factory and the H. Upmann brand was launched.[1]

Upmann is sometimes credited with the invention of packaging cigars in cedar boxes to give to their customers. These original boxes were labelled with the H. Upmann name and contained other manufacturers' cigars, most likely as an advertisement for the operation, until the Upmanns bought their own cigar factory in 1844: the famous H. Upmann Factory, now known as the José Martí Factory, in Havana. In another version of the story, it was the Upmann brothers' nephews, German and Alberto, who founded the factory and the cigars became associated with it.

Through the late 1800s, the H. Upmann brand gained international recognition at various exhibitions and won seven gold medals which still adorn the lithographed art on today's H. Upmann boxes, along with Hermann Upmann's original signature.

In 1922 both the H. Upmann Bank and the cigar business went bankrupt, the bank because of speculation in German marks and Mexican oil properties.[1][2] A British firm, J. Frankau & Co., bought the brand name and continued production until 1935, when the company was sold to the recently established Menéndez, García y Cía Co., makers of the Montecristo brand.[1] This new ownership group continued production of H. Upmann cigars until the nationalization of the tobacco industry after the Cuban Revolution.

After the revolution, Menéndez and García moved the brand first to the Canary Islands, then the Dominican Republic, where production continues for the American market (due to the Cuban embargo) under the ownership of Altadis SA, while the original brand remains in the original factory, now known as the José Martí Factory, in Havana, still using tobacco from the premium Vuelta Abajo region.

One of the labels used by Altadis for its non-Cuban H. Upmann cigars.

The Cuban-made brand still remains a popular cigar on the world market, where it is made in a variety of hand-made as well as machine-made vitolas. In 2002, when Altadis SA bought a controlling share in Habanos SA, numerous changes were made to the H. Upmann lineup, with the vast array of more than 30 vitolas rationalized so that redundant and poor selling sizes were eliminated.[1] By 2006, according to the company, the H. Upmann line had been whittled down to just 16 vitolas.[4]

In 2005, Habanos SA made an unexpected move by offering a new H. Upmann as part of their annual Edición Limitada release. This was uncharacteristic because in the past the limited edition releases had only been produced for their five globally distributed brands (Cohíba, Montecristo, Romeo y Julieta, Partagás and Hoyo de Monterrey), whereas the non-Cuban H. Upmann was a locally-distributed brand. The limited edition size was a large Magnum 50, thought to be an enticement to smokers who enjoy the Magnum 46. Shortly after, Quintero was demoted to a locally-distributed brand in the Habanos portfolio, while H. Upmann was raised to a global brand with distribution in every nation that imports Habanos cigars.

H. Upmann also produces two machine-made cigarillos (the Mini and the Purito) and a brand of cigarettes under the direction of ICT.

A double guillotine-style cutter, used for cutting the tip off a cigar, next to two hand-rolled H. Upmann Coronas Major cigars, one inside its storage tube and one outside.

The following list of handmade vitolas de salida (commercial vitolas) within the H. Upmann marque lists in order, their length in Imperial (and Metric), ring gauge, their Factory name, a colloquial description of size/shape, (release date and current manufacture):